SYNTHESIS AND ABSOLUTE-CONFIGURATION OF (+)-HAPALINDOLE-Q

被引:75
作者
VAILLANCOURT, V [1 ]
ALBIZATI, KF [1 ]
机构
[1] WAYNE STATE UNIV,DEPT CHEM,DETROIT,MI 48202
关键词
D O I
10.1021/ja00062a013
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The versatility of brominated camphor derivatives as six-membered-ring chiral building blocks in the synthesis of compounds of mixed biogenesis has been demonstrated in an eight-step synthesis of (+)-hapalindole Q from (+)-(1R)-9-bromocamphor in an overall 8% yield which confirms the absolute stereochemistry to be 10R, 11R, 12R, 15R.
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页码:3499 / 3502
页数:4
相关论文
共 25 条
[1]   ACID-CATALYZED REACTIONS OF HAPALINDOLES [J].
BONJOUKLIAN, R ;
MOORE, RE ;
PATTERSON, GML .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (25) :5866-5870
[2]   MARINE NATURAL-PRODUCTS [J].
FAULKNER, DJ .
NATURAL PRODUCT REPORTS, 1991, 8 (02) :97-147
[3]   PALLADIUM-CATALYZED COUPLING OF 3-INDOLYL TRIFLATE - SYNTHESES OF 3-VINYLINDOLES AND 3-ALKYNYLINDOLES [J].
GRIBBLE, GW ;
CONWAY, SC .
SYNTHETIC COMMUNICATIONS, 1992, 22 (15) :2129-2141
[4]   PALLADIUM-CATALYZED REACTIONS IN THE SYNTHESIS OF 3-SUBSTITUTED AND 4-SUBSTITUTED INDOLES - APPROACHES TO ERGOT ALKALOIDS [J].
HARRINGTON, PJ ;
HEGEDUS, LS .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (15) :2657-2662
[5]   PALLADIUM-CATALYZED REACTIONS IN THE SYNTHESIS OF 3-SUBSTITUTED AND 4-SUBSTITUTED INDOLES .2. TOTAL SYNTHESIS OF THE N-ACETYL METHYL-ESTER OF (+/-)-CLAVICIPITIC ACIDS [J].
HARRINGTON, PJ ;
HEGEDUS, LS ;
MCDANIEL, KF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (14) :4335-4338
[6]  
JOSHI GC, 1967, TETRAHEDRON LETT, P3613
[7]   ALPHA-PHENYLATION OF KETONES VIA TIN ENOLATES CATALYZED BY A PALLADIUM COMPLEX [J].
KOSUGI, M ;
HAGIWARA, I ;
SUMIYA, T ;
MIGITA, T .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1983, (07) :344-345
[8]   ARYLATION AND 1-ALKENYLATION ON ALPHA-POSITION OF KETONES VIA TRIBUTYLTIN ENOLATES CATALYZED BY PALLADIUM COMPLEX [J].
KOSUGI, M ;
HAGIWARA, I ;
SUMIYA, T ;
MIGITA, T .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1984, 57 (01) :242-246
[9]   SECOHEXAPRISMANE [J].
MEHTA, G ;
PADMA, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (07) :2212-2213
[10]   AN INTERESTING CHLORIDE-ION EFFECT IN THE HECK REACTION [J].
MERLIC, CA ;
SEMMELHACK, MF .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1990, 391 (02) :C23-C27